10 Great Date Night Ideas In Boston, Massachusetts - Updated 2024

date night ideas in boston
Contributing Writer
| 4 min read

Boston is a city full of life, art, and culture. This vibrant capital city is also most populated in the state of Massachusetts. It is famous for the annual Boston marathon event that is always held on the 3rd Monday of April. Other attraction sites include the historic Fenway Park, New England Aquarium, Old State House Museum, Boston Tea Party Ships and Museum, and the Freedom Trail — a favorite among tourists and a popular route with beautiful historic sites and museum. Tourist attractions are just a tip of the iceberg, since Boston is also known for its range of inviting restaurants with unique dishes. Read on to know more about great date night ideas in Boston, Massachusetts.

1. Watch a theatrical show at Calderwood Pavilion

MacKenzie Meehan, Kathleen McElfresh, and Christopher Donahue in the Huntington Theatre Company production of the moving Irish drama The Second Girl by Ronan Noone, directed by Campbell Scott, playing January 16 – February 21, 2015 at the South End/Calder
Source: Photo by user The Huntington used under CC BY 2.0

When it comes to entertainment, Calderwood Pavilion is famous for entertaining audiences with theatrical shows ranging from classics to new work productions. Prepare to get immersed in live shows that bring life to a story, capturing your attention and engaging you as if you are the character in the show. Be the first to grab a ticket and pick the best seat to enjoy a show performed by the city’s best artists.

Calderwood Pavilion

Address: 527 Tremont St, Boston, MA 02116

Website: Calderwood Pavilion

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2. Watch the skies at Coit Observatory's Public Open Night

date night ideas in boston | watch the skies at coit observatory's public open night
Source: instagram

If you love watching the sky at night or you dream of exploring the stars, you have to experience a public open night at the Coit Observatory. This is where you get front-row seats to observe the beautiful night skies through the telescopes. Although it is a free activity, space is limited, so it is good to have your ticket reserved early enough. This event presents the perfect activity for a romantic evening or an amazing chill spot for astronomy fans.

Coit Observatory

Address: 725 Commonwealth Avenue, Boston, MA 02215

Website: Coit Observatory

Price: Free

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3. Crack a rib at Laugh Boston's comedy night show

Editor's Note: Photo taken from the establishment's official social account

If you are feeling down and want something to cheer you up, why not get a dose of laughter at Laugh Boston. This premier comedy club offers a state-of-the-art chilling spot where all types of comedians gather to fill the air with jokes and laughter. A light-fare menu will fill your bellies with tasty food, and if you are tensed or stressed, the bar offers a wide range of drinks to ease your nerves.

Laugh Boston

Address:425 Summer St, Boston, MA 02210, United States

Website: Laugh Boston

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4. Enjoy a romantic Odyssey Dinner Cruise (from USD 137.0)

If you are looking to try out something different from a typical night-out, the Boston Odyssey Dinner Cruise has something interesting for you to experience. On this three-hour cruise, the observation deck offers breathtaking views of Boston Harbor and the setting sun. After enjoying a three-course dinner, stroll under the stars sipping wine as you marvel at Boston’s skyline illuminated at night. If you still have some energy left, head inside to the ship’s nightclub for some fun live entertainment and dancing.

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Boston Premier Dinner Cruise on Odyssey

Duration: 2 hours 30 minutes

127 reviews

Boston Tour Guide

Naim Benmayor

Naim Benmayor

As a Boston tour guide, I have the added experience of being a world traveler. For many years, I frequently visited Europe, Asia, and Latin America on business. During this time, I also organized tours of the USA, Europe and Asia for my business clients. I now bring this passion, excitement and expertise to the Boston area.By exploring the globe, I was exposed to various cultures, and this uniq... Read more

5. Go for dinner and cocktails at Yvonne's

Editor's Note: Photo taken from the establishment's official social account

From its polished décor, warm ambiance to posh comfort, all features in Yvonne’s emanates a refined yet playful vibe. Yvonne’s is a restaurant and a stylish diner club with a concealed entrance behind a discrete bookshelf — it’s a very private club, indeed. At the mahogany bar, an array of crafted beer, cocktails, and sophisticated wine collections will quench your thirst while the music sets the mood for an exciting night-out. With only seven dining tables available, be the first to reserve your space in this upscale diner club.


Address: 2 Winter Pl, Boston, MA 02108, United States

Website: Yvonne’s

Opening hours: 5:00pm – 11:00pm; 4:00pm – 2:00am (daily)

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6. A night at the Isabella Stewart Gardner Museum

Courtyard, Isabella Stewart Gardner Museum, Boston
Source: Photo by user Sean Dungan used under CC BY-SA 4.0

If you are looking for a late-night activity that is somewhat unorthodox, why not do a late-night visit to a museum? The Isabella Stewart Gardner Museum houses a collection of sculptures, paintings, decorative arts, tapestries, and paintings. The museum offers a chance to explore and marvel at exhibits of Asian, American, and European art at night, as well as a romantic after-dinner night tour for lovebirds.

Isabella Stewart Gardner Museum

Address: 25 Evans Way, Boston, MA 02115

Website: Isabella Stewart Gardner Museum

Opening hours: Fri - Mon: 11am - 5pm; Wed: 11am -5pm; Thurs: 11am - 9pm (closed on Tue)

Price: Adults: USD 15; Seniors: USD 12; Students: USD 10

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7. Embark on an hour expedition of the famous Boch Center - Wang Theatre (from USD 25.0)

On this one-hour expedition, you get to tour one of the city’s most famous landmarks. Since its opening in 1925, the Wang Theater has been a premier theater that has hosted renowned artists including Lady Gaga, Queen, Benny Goodman, and Janet Jackson. It is one of the five largest stages in the country and accommodates guests of all ages. A behind-the-scenes tour of this prominent landmark is one of the best ways to spend a casual night in Boston.

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Boston Boch Center Wang Theatre Group Tour

Duration: 1 hour 15 minutes

92 reviews

8. Tour Boston's waterfront on a Sunset Cruise (from USD 116.0)

Late nights must not involve drinking and partying all the time. You can choose an alternative route and opt for a more relaxed evening at Sunset Cruise. Enjoy an exhilarating dinner cruise gorging yourself on all-you-can-eat buffet as you sail along Boston’s waterfront. Start your evening by watching the sunset or enjoying the scenic view of Boston, which is illuminated at night. Burst your moves on the dance floor of the ship’s nightclub located inside the boat.

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Boston Signature Dinner Cruise

Duration: 2 hours 30 minutes

204 reviews

9. Watch the Blue Man Group at the Charles Playhouse (from USD 85.0)

Boston nights always feels short because of so many activities to do but so little time to do them. Charles Playhouse offers a venue where you can utilize at least two hours of your night-time. Here is where you can come to witness the Blue Man Group performance for yourself. The Blue Man Group is the city’s longest-running show, which an exciting family-friendly experience for those who come to play at night. The show has amalgamated, humorous musical arts and experimental music. As a result, the group produces the best night shows in the city.

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Blue Man Group Boston Admission at the Charles Playhouse

Duration: 1 hour 30 minutes

19 reviews

10. Enjoy a relaxed harbor night cruise (from USD 26.0)

During the day, the streets of Boston are full of life as people engage in different activities while at night, the city transforms into a spectacle illuminated by building lights. On this one-hour night cruise, you get to sail past the Independence Wharf, Old North Church, U.S.S. Constitution, and the New England Aquarium. You can choose to stay warm and cozy in the interior cabin, or if you love the open air, the top deck is equipped with blankets.

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Boston Harbor Night Cruise

Duration: 1 hour

2 reviews

Explore Boston’s nightlife

When the sun sets, that doesn’t mean that everything stops. Contrary to that, when other businesses close, more businesses open, adding fuel to the Boston’s city life. There is a beauty in the night when the skies are illuminated by city lights. The night is also when people feel free to release their stress. To do so, you need to know where to go. This list has summed up the best places to visit depending on the mood and vibe of the day. With this list of Boston’s night venues and ideas, you are all set.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Hi, David Kross is my name. I'm an energetic writer in love with traveling and always seeking new adventures. I love to share my story and experience with anyone who is like-minded or seeking new...Read more

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